My mom is finally beginning to clear out some of her homeschooling resources (with her youngest kid now 21, the need is clearly past, and with over 5000 other books, space is limited) and so during my recent visits I've taken home some of the potential discards that we plan to use ourselves eventually.
Among these is a copy of Laura Berquist's book Designing Your Own Classical Curriculum. Right now MrsDarwin and I are looking for ideas on good resources for teaching reading and very basic arithmetic, as the oldest monkey approaches four and it seems like time to get started on such things before too much longer.
We may well end up using some of the resources she mentions in those earlier grades (one of our challenges is that we mostly only have opinions about education in the later years, say 4th grade plus.) However, reading through the rest of the book, I'm reminded of some of the issues I had with the book when I read parts of it back when it came out ten years ago, reading it as a homeschooler in the latter years of high school.
Berquist's aim is provide a basic classical education that will then allow the student to go on to a small Catholic liberal arts college, specifically Thomas Aquinas College in California, which has a program based solely on the Great Books model. (Berquist herself went to TAC and she mentions in the book that her oldest child had just been admitted there.)
I think there's a lot of good to be found in reading the Great Books at a college level. (MrsDarwin and I both took part in Steubenville's Great Books-based Honors Program, which made up one of our five classes every semester throughout college and got a bunch of our core requirements out of the way.) However, doing nothing but the Great Books in college seems to me to be a mistake. I think it's important to have an academic major, belong to a department, and do at least a little bit of in-depth study (a thesis or senior project) while getting your bachelor's degree. It's especially important to do independent research and become more expert on a few specific areas of study within your field than your professors are.
The approach that my parents took, which we hope to emulate with our own children, was to provide a solid basic education by the end of eighth grade (essentially doing in K-8 what Berquist does in K-12) and then work through a unified humanities (history, literature, philosophy and theology all rolled into one) program in 9-12, while doing college prep math, science and foreign language as separate subjects. Certainly, a 14-year-old isn't old enough to get all there is to get in Homer, Plato, Virgil and Cicero, nor is a 16-year-old going to understand all there is to know about Aquinas, Dante or Thomas More, but they are old enough to give it a decent shot, and if they encounter those authors again in a more advanced setting, they'll be able to get much more out of it on a second go-around.
Indeed, I think you're pretty much guaranteed not to "get" these authors fully on a first read (in college or high school) so it's best to get the first, unenlightened pass out of the way early. And although I may not have come out of the humanities program knowing everything there is to know about the works I'd read, I certainly think I was far better off for having read them.
Now clearly, your kid needs to be a reading powerhouse by 9th grade to push through stuff like the Iliad in a reasonable period of time, but if you've been homeschooled through eighth grade that shouldn't exactly be a problem. (It helps to be already familiar with the story, either from hearing it read aloud or from reading an abbreviated version at a younger age.)
Right now, however, we're mostly in search of good materials for teaching reading in the first place, plus some added inspiration on chapter books that would be interesting read-alouds for the monkeys (Little House in the Big Woods was a big hit, but we're not sure if the other Laura books might still be a bit over their heads, so we're looking for new ideas, since nothing currently on my self seems to be a good fit, unless perhaps Charlotte's Web.) and in that regard Berquist's book looks like it may have some good leads.